One of our greatest pleasure is watching those scoundrels out there smart enough to pull one over on the smartest of businessmen, government officials or the like. That mixed with a story that outsmarts us and together you get a great Con movie. For decades, great pieces have come out and they continue to hold up because of the universal themes that we love. Below you will find the absolute 28 best con movies of all time.
#28 The Brothers Bloom
The all-star cast of Rachel Weisz, Adrien Brody and Mark Ruffalo is about the fabled Brothers Bloom who were the best Con Men in all the land. After much success they plan to take one more job, getting into it with the beautiful and crazy heiress. As you would assume, hilarity and misfortune follow. While not one of the best con movies of all time, it is a very fun ride with people you love, just getting this gem onto the list.
#27 Six Degrees of Separation
Even though this is one of his first theatrical performances, Will Smith gives a powerhouse performance in this film about a strange man who charms his way into the home of wealthy New York art dealers and is never who he seems. Also starring Stockard Channing and Donald Sutherland, this thriller keeps you on the seat of your pants and stays with you.
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#26 Mo’ Money
At the peak of his career, Damon Wayans made the action-comedy Mo’ Money about a small-time con man who tries to go legitimate after falling in love with Stacy Dash. With a new career at a credit card company he, unfortunately, gets even more in over his head and finds himself the only man who can take down a con the likes even he has ever seen.
Rachel Weiss makes her second appearance on the list of best con movies but this time with an older gem that also starred Edward Burns, Dustin Hoffman and Paul Giamatti. Confidence is a film about a grifter, played by Burns, and his gang of cons who want to do one that job that will avenge a friend. Unfortunately for them it all goes to hell and the mob boss played by Hoffman is less than happy about it. This gritty grifter film has plenty of attitude and will keep you engaged from start to finish.
Based on the real-life story of MIT students who formed an underground blackjack card counting ring to take Vegas for hundreds of thousands of dollars, Director Robert Luketic does a fantastic job of inserting style and suspense into this one-note story about math. Kevin Spacey, who we realize now should have been never allowed to make movie after movie with kids, is the teacher turned villain in a character arc you never really know who he is, making for one of the best con movies out there.
#23 The Two Faces of January
That’s right, the incredibly talented Viggo Mortensen and Oscar Isaac did a movie together! Kirsten Dunst is in it too. That should be enough but there is so much more. The film has plot twist after twist and of coarse no one is as they seem. This is one of the more obscure less known entries on the list of best con movies.
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This film gets its name from the boxing town of the same name that it centers around. Louis Gossett Jr. plays and over the hill and pawn in a bet between businessmen Bruce Dern and James Woods. This smart sports drama is always exciting and always interesting. Though great, you may have missed this one because it was one of 9 sports-related movies to come out in 1992.
#21 The Grifters
This one is about con man John Cusack being torn between the two women in his life, his mother played by Anjelica Houston and his girlfriend played by Annette Bening. As you can guess, each character has their own grift they are playing and their own motivations and their own secrets. Twists and turns come from all directions in this thrilling drama. All three key cast members give great roles in ways that you wouldn’t normally see. Everything together puts this one on the list of best con movies.
#20 Boiler Room
The term “boiler room” refers to the real-life call centers in the 80s – 90s where groups of young confident salesmen/stockbrokers call people and engage in different stock scams. Mainly the pump and dump which is where you buy garbage stock at nothing, you convince everyone it is great so the stock price goes out and then you sell off all the garbage stock to make a killing, leaving the unsuspecting duped citizen with worthless stock and no money. Take that exciting concept and add some hot up and comers like Giovanni Ribisi, Scott Caan and Vin Diesel, and you got your self a pretty exciting film and a slam dunk for the list of best con movies.
#19 The Distinguished Gentleman
You would think that a list of the best con movies would have more politically themed entries, but this is the only one. Eddie Murphy is a small town con-man who through a crazy circumstance and subsequent con ends up in Congress. The rub is that everyone there is a much better con man than him, but in Washington DC it is legal, its called being a politician. He cooks up a fun plan that is both entertaining and very satisfying.
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#18 Matchstick Men
This dry and stylish con man movie from director Ridley Scott is both star-studded and well written. A con man played by a germaphobic Nicolas Cage finds out he has a daughter and it changes his life. While this is happening, there are some things happening that you would never seen coming that make for one incredible payoff. While other films on the list of best con movies only have some cons in them, this movie is so much about con men that it deserves bonus points.
When you think smooth and charming, you immediately go to Will Smith and that is for good reason, he very much is those things. This is another film on the list of best con movies that is actually about a con man. His past intertwines with his present making for a few complicated problems that need to be solved. The beautiful and magnetic Margot Robbie is the female lead and was such a good counterpoint to Will.
#16 Jackie Brown
Director Quentin Tarantino wanted to throwback to the amazing cinema movement that was black exploitation. To lead this elaborate con-man caper he taped Pam Grier who could not have been a better choice. She is an older woman but still kicking ass and looking good doing it. Like all Tarantino films, it goes all-in on style, performances, and storytelling, and does not disappoint.
#15 The Color of Money
Tom Cruise and Paul Newman is the perfect mix of old school and new school in this con-man movie about pool hustling. Not only is it cool but it has lots of heart. Paul Newman stars as washed up and Tom Cruise stars as cocky and sloppy, together they made each other great again. This one has easily held up to the test of time as far as best con movies go. It also helped that it had the perfect director in the great Martin Scorsese.
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#14 White Men Can’t Jump
When just hearing the title “White Men Can’t Jump” you would never think this would be a big deal theatrical movie but it was and it delivered. This as all about the unlikely pair of basketball hustlers, Wesley Snipes and Woody Harrelson, who start as enemies but of coarse end as friends. The dialogue and their chemistry are enough to make this an instant classic, but the story and art of their hustle keeps you glued to the narrative.
Maverick is a very fun, lively, commercial, white bread take on the wild west. It is popcorn entertainment with great interweaving performances from Mel Gibson, Jodie Foster and James Garner. These outlaw poker players that each have their own checkered past have a lot of fun trying to pull one over on each other, and the audience has it with them. Director Richard Donner was the mastermind behind this entry on the list of best con movies.
From ultra-cool director Guy Richie comes a film that brings together violent bookmakers, a Russian gangster, unethical boxing promoters and supposedly Jewish jewelers all on a hunt for a stolen diamond in the heart of the UK underground. A who done it packed with the grit and swag, a fun and exciting ride. This entry into best con movies marks some of the earliest performances from talents like Brad Pitt and Jason Statham.
#11 Paper Moon
The only black and white film on the list of best con movies, Paper Moon was made in 1973 and stars father-daughter team Tatum O’Neal and Ryan O’Neal. Ryan was one of the biggest things in the world at the time, she would go on to win a best-supporting actress Oscar for this performance, the youngest woman in history, and would later be the highest child paid actor of all time for her 1976 role in Bad News Bears. Paper Moon has always been a best con movies classic, and several would say that it invented the door to door grifter game.
#10 Identity Theft
Part road trip movie, part Melissa McCarthy comedy and part con movie, Identity theft is truly a funny funny smart funny film. This two-hander follows a cooky con woman and a man whose identity she stole on a chase across the US. Both McCarthy and male lead Jason Bateman are at their best and the storytelling is top-notch, both in heart and humor. A slam dunk on the list of top con movies but don’t be surprised if this one shows up on a few other lists.
#09 The Producers (1967)
Our only film that looks behind the making of entertainment to the obvious con man, the producer. This odd couple story pairs eccentric less than ethical b-level play producer and by the books auditing accountant in a scheme to oversell the ownership of a movie to investors and then purposefully make a terrible movie so no one realizes it. They find “Springtime for Hitler” the musical comedy, but no matter hard how they try they can’t seem to make it a flop. This film was so ahead of its time, it started a few storytelling tactics that are still along today. The movie was so good, it was made into a Broadway show and then that was made into a movie.
#08 Dirty Rotten Scoundrels
In 1988, Steven Martin was coming off being one of the biggest comedians in the world and Michael Cain was coming off being one of the biggest charming sex icons and actors in the world. Together they joined forces and made this classic crime comedy about two men fighting over the same woman. Both men are different kinds of con men who both are arrogant enough to think they will beat the other, but in the end, it doesn’t end up how either of them imagined it would.
#07 American Hustle
David O’Russell followed up his critical darlings Silver Linings Playbook and the Fighter with a very ambitious film about a pair of con men forced with to work with the F.B.I. to take down corrupt government officials. Though it is a period film, it is the adult ensemble caper for this generation. This film has Christian Bale, Amy Adams, Bradley Cooper, Jeremy Renner and Jennifer Lawrence. Those are some of the best actors of this generation, and no one had brought them all together before. David did and he did it well, this film had so much style and was told to us so well. This will definitely be one of the classics of the best con movies and will live on for years to come.
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#06 Trading Places
Even though #6 on the list of best con movies, this film gets the #1 movie for standing the test of time. You can pop this 1983 film on the tv and it is just as fresh and relevant today. Eddie Murphy and Dan Ackroyd give performances of a lifetime as a poor con man and wealthy businessmen that are made to switch stations in life to see what would happen. They learn the truth and join forces to take down the businessmen playing the cruel trick on them. The film is charming, funny and it is one hell of a story. Universities teach classes on how good this film is.
This beautiful stylish thinker is the only film on the list not to be based in reality as we know it. When Inception came out, the world collectively scratched their heads. It is so simple yet so complex, with layer after layer after layer of complexities, but people came around. This story is still held up as one of the more magical stories ever told and it was brought to the world by one of the greatest directors of all time, Christopher Nolan. The basic gist is there is a way to invade someone’s dreams to make them suggestible to ideas, but people’s heads can be very complex and dangerous places to be. Even reality is a con man.
#04 Catch Me if You Can
Steven Spielberg should get a casting of the century award for putting together Leonardo DiCaprio as real-life youthful con man Frank Abignale Jr. and Tom Hanks as Agent Carl Hanratty. Their life long cat and mouse game was both warm and fun to watch. Frank comes up with brilliant scam after brilliant scam, and Hanratty is always one step behind. It is beautiful how it all comes together and with amazing performances, amazing direction and an amazing story, no wonder this classic makes it so high on the list of best con movies of all time.
#03 Wall Street
Greed is good. This is the motto of Gordon Gecko, the super-villain stock trader played by Michael Douglas. Douglas won the best actor oscar for this performance and for good reason, it is this writer’s opinion that this performance is the best villain ever portrayed since the beginning of cinema. It will blow you away how intense his performance is and how unbelievably that a wolf of a con man could hide in such plain sight. Charlie Sheen is actually very good as well, but it is the masterhood of Michael Douglas that makes this one of the best con movies of all time.
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#02 Glengarry Glen Ross
Glengarry Glen Ross is one on the list of best con movies that is actually revolutionary, not just a great ride. Everything on this list is noteworthy but GGGR deserves a special place in history. It has one of the most shrewdly intertwined ensemble cast in Al Pacino, Jack Lemmon, Alec Baldwin, Alan Arkin, Ed Harris and Kevin Spacey. Everyone mixes together so well and everyone gave A+ performances. That mixed with an incredibly dark and tormented story and some iconic moments (think ABC, Always Be Closing) all together make an iconic cinematic classic that is a time capsule to a pristine moment.
#01 The Sting
After 40+ years, this Paul Newman Robert Redford Con Movie still holds up. After everything that has come out since this masterpiece has stood the test of time and still deserves to be #1 on the list of top con movies. The big con here is they delay the reporting of a horse match and get in there just before so it makes it look like to the mark that they have the answers. Just on the surface though. Your entire grasp on reality gets thrown upside down over and over in this fun caper. The Sting won 7 academy awards including best picture, and that was not by mistake.